The Playboy Interview: A Candid Conversation with Gawker's Nick Denton

Manti Te'o had a fake girlfriend. Rob Ford smoked crack. Brett Favre texted photos of his junk to a young woman. That these and countless other onetime secrets are now public knowledge is thanks to Nick Denton, the founder and owner of a network of news-and-gossip websites called Gawker Media. When Denton, a U.K.-reared financial journalist, founded it in 2002, he was already a successful entrepreneur twice over, having started and sold First Tuesday, which produced networking parties for young professionals in technology and related fields, and Moreover Technologies, which automated the process of aggregating news headlines for websites. The two sales netted around $90 million.

Denton's third company started with Gizmodo, a gadget blog, then blossomed with the launch of Gawker, a nasty and funny blog about New York's cultural and financial elite as viewed by the resentful underclass.* A sensation from its launch, it spawned sister sites covering sports (Deadspin), women's issues (Jezebel) and other subjects. Operating outside the journalistic establishment and its constraints, Gawker Media writers were the first to break the scandals around Te'o, Ford and Favre. They also published the photo that forced "Craigslist congressman" Chris Lee to resign and got their hands on a prototype of the then top-secret iPhone 4—a scoop that drew considerable heat from law enforcement and a furious personal response from Steve Jobs.

Despite the hundreds of millions of page views these and other stories have yielded—translating into an estimated $40 million in annual ad revenue—Denton isn't satisfied. Gawker's reliance on journalists is, he believes, a fatal weakness, one he means to correct with a new system called Kinja, which he is currently in the process of refining. Part publishing platform, part social network, Kinja aims to do nothing less than turn Gawker Media's 80 million monthly readers into willing accomplices, a virtual nation of gossip reporters. In fact, Playboy is also an accomplice, regularly republishing articles from both the magazine and its digital platforms on Kinja.

To pry secrets out of the man who exposes the secrets of others, Playboy tapped respected media writer Jeff Bercovici. He reports: "When I first sat down with Denton, he had some personal news he was happy to share: He had just gotten engaged to his boyfriend, Derrence Washington, a handsome African American actor. The two live together in a vast and somewhat severe loft apartment in SoHo, where we conducted much of this interview (when we weren't eating Thai food at a nearby restaurant). A trim 46, Denton dresses in casual but stylish clothes of gray and black and keeps his salt-and-pepper hair cropped short. Feared and reviled by so many, in person he is candid and voluble, with no shortage of opinions and no fear about betraying his own privacy."


PLAYBOY: You've said the mission of Gawker is to publish the stories that journalists talk about with one another in private but never write.

DENTON: Yeah, the founding myth of Gawker happens to be true. I was a journalist at the Financial Times. Whenever you work at a newspaper, particularly a newspaper with high standards, you're struck by the gap between the story that appears in the paper the next day and what the journalist who wrote that story will tell you about it after deadline. The version they tell over a drink is much more interesting—legally riskier, sometimes more trivial, and sometimes it fits less neatly into the institution's narrative. Usually it's a lot truer. The very fact that a journalist will ask another journalist who has a story in the paper, "So what really happened?"—now, just think about that question. It's a powerful question. It's the essence of all meaningful gossip. That's why this discussion system, Kinja, is so important. It actually allows us to fulfill our original objective, which is to treat everybody equally, to find interesting stories wherever they are, not just if a celebrity is involved. That's not economical with paid journalists doing all the work. We need reader help. If we're covering you, we need your colleagues to rat you out or your exes to put in bits and pieces. It has to be a collaborative effort.

PLAYBOY: So Kinja is your bet that in 10 years we will all be part of a crowdsourced gossip press reporting on one another.

DENTON: The Panopticon—the prison in which everybody is exposed to scrutiny all the time. Do you remember the website Fucked Company? It was big in about 2000, 2001. I was CEO of Moreover Technologies at the time. A saleswoman put in an anonymous report to the site about my having paid for the eye operation of a young male executive I had the hots for. The story, like many stories, was roughly half true. Yes, there was a young male executive. Yes, he did have an eye operation. No, it wasn't paid for by me. It was paid for by the company's health insurance according to normal procedure. And no, I didn't fancy him; I detested him. It's such a great example of Fucked Company and, by extension, most internet discussion systems. There's some real truth that gets told that is never of a scale to warrant mainstream media attention, and there's also no mechanism for fact-checking, no mechanism to actually converge on some real truth. It's out there. Half of it's right. Half of it's wrong. You don't know which half is which. What if we could develop a system for collaboratively reaching the truth? Sources and subjects and writers and editors and readers and casual armchair experts asking questions and answering them, with follow-ups and rebuttals. What if we could actually have a journalistic process that didn't require paid journalists and tape recorders and the cost of a traditional journalistic operation? You could actually uncover everything—every abusive executive, every corrupt eye operation.

PLAYBOY: What are the implications for the broader society? What does America look like from inside the Panopticon?

DENTON: When people take a look at the change in attitudes toward gay rights or gay marriage, they talk about the example of people who came out, celebrities who came out. That has a pretty powerful effect. But even more powerful are all the friends and relatives, people you know. When it's no longer some weird group of faggots on Christopher Street but actually people you know, that's when attitudes change, and my presumption is the internet is going to be a big part of that. You're going to be bombarded with news you wouldn't necessarily have consumed—information, humanity, texture. I think Facebook, more than anything else, and the internet have been responsible for a large part of the liberalization of the past five or 10 years when it comes to sex, when it comes to drinking. Five years ago it was embarrassing when somebody had photographs of somebody drunk as a student. There was actually a discussion about whether a whole generation of kids had damaged their career prospects because they put up too much information about themselves in social media. What actually happened was that institutions and organizations changed, and frankly any organization that didn't change was going to handicap itself because everyone, every normal person, gets drunk in college. There are stupid pictures or sex pictures of pretty much everybody. And if those things are leaked or deliberately shared, I think the effect is to change the institutions rather than to damage the individuals. The internet is a secret-spilling machine, and the spilling of secrets has been very healthy for a lot of people's lives.

PLAYBOY: The secret-spilling-machine part seems self-evident. As for the liberalizing part, there's a lot of data that says essentially the more information people have, the more entrenched they become in their own views—the more they suffer from confirmation bias.

DENTON: Obviously sometimes you go on Facebook and it's totally one-note and there's no real discussion or argument. You can have a debate on Twitter, but I've never seen anyone persuaded there. Twitter is bad for our intellectual health. That's something I would like to do something about. It would be nice to have a civil place for argument. It should be like a good seminar—in an English university, where people actually disagree, not an American one.

PLAYBOY: Is it possible you set a lower value on privacy than most people do?

DENTON: I don't think people give a fuck, actually. There was a moment when I thought some sex pictures of me were about to land. Someone claimed to have some and to be marketing them. I even thought I knew where they'd come from—I'd lost a phone. But it turned out to be a hoax.

PLAYBOY: And you weren't freaked out?

DENTON: It would have been mortifying, but every infringement of privacy is sort of liberating. Afterward, you have less to lose; you're a freer person. Shouldn't we all want to own our own story?

PLAYBOY: You're more willing than most people to organize your life according to principle and see how the experiment turns out.

DENTON: You could argue that privacy has never really existed. Usually people's friends or others in the village had a pretty good idea what was going on. You could look at this as the resurrection of or a return to the essential nature of human existence: We were surrounded by obvious scandal throughout most of human existence, when everybody knew everything. Then there was a brief period when people moved to the cities and social connections were frayed, and there was a brief period of sufficient anonymity to allow for transgressive behavior no one ever found out about. That brief era is now coming to an end.

PLAYBOY: That doesn't jibe with your other theory about how we'll judge one another more kindly when we have no privacy. Human history is not a history of tolerance for deviation from the norm.

DENTON: You don't think there was a kind of peasant realism? You hear these stories about a small town, seemingly conservative, and actually there's a surprising amount of tolerance. "So-and-so's a good guy. Who cares if he's a pig fucker? His wife brought a really lovely pie over when Mama was sick."

PLAYBOY: Do you feel the same about the dilution of our privacy rights when governments are doing it?

DENTON: I feel there are certain efficiency gains, at least in the merging of government databases. But that needs to be counterbalanced by a reciprocal openness on the part of government.

PLAYBOY: So you're okay with the NSA listening to your phone calls as long as you can listen to the NSA's phone calls.

DENTON: I suppose that would be the extreme manifestation.

PLAYBOY: For someone who is half-jokingly referred to as the Dark Lord by employees, you're surprisingly optimistic, even utopian, about the future.

DENTON: I am totally earnest.

PLAYBOY: What do you think about the critique that the technology industry does an amazing job solving the problems of affluent people—especially affluent men in their 20s and 30s, who make up most of that industry's workforce—and a pretty crappy job of solving everybody else's problems?

DENTON: It's a good point but wrongheaded. Look at Steve Jobs. Did he or did he not advance human civilization? Was he not an agent of progress? He's like one of those Victorian figures. That's the tradition he's in. How many of those were there in the late 20th century? Who was big in the 1980s? It was financial engineers, people like John Malone and Barry Diller. Now, through technology, there's a new generation of builders. Evan Williams of Blogger and Twitter, Larry Page and Sergey Brin of Google, Jeff Bezos of Amazon and of course Steve Jobs.

PLAYBOY: Would you say Steve Jobs is one of your heroes?

DENTON: Yeah, absolutely.

PLAYBOY: And yet you famously antagonized him, buying a prototype of an iPhone 4 that an Apple engineer had misplaced months before it was ready for release, and you published pictures and video of it. What exactly happened?

DENTON: We've always advertised our willingness to pay for information, which is why we were approached when somebody picked up an iPhone 4 prototype in a bar. We negotiated with the people who had the phone. It was a huge break—the first time Apple's very controlled rollout had been derailed by an accident. I forget how much we paid. It was cheap. It was a crazy story. Steve Jobs was on the phone to the editor of Gizmodo, saying, "Give me my fucking phone back." We did two weeks of coverage. The journalist who had seen the phone and reported the story about Apple's secret prototype had his apartment broken into.

PLAYBOY: Broken into?

DENTON: By police. It was Apple's pet police force, some computer task force in Silicon Valley that is notoriously close to the tech industry. It was a great story.

PLAYBOY: Did it bother you, knowing that one of your heroes pretty much hated your guts?

DENTON: He does his job; we do our job. His perfect thing requires both excellence in engineering and user interface and absolute control of the marketing process so that when he goes onstage, his product is a surprise. And our purpose is at odds with his purpose. Our purpose is to get information out quickly according to our schedule, not according to his schedule. So there's a conflict. It doesn't mean we don't respect him. We did respect him.

PLAYBOY: What do you think of his successor, Tim Cook?

DENTON: He has a hard act to follow.

PLAYBOY: Your websites have repeatedly harped on him for being gay but not publicly out. Why?

DENTON: I mean, it's not as if there's anything at all in his public persona or in his pronouncements that is necessarily at odds with his private homosexuality, but I think it would be useful. It would be socially useful for the most powerful man in American business to be seen and widely known as being gay. People would see that if you're gay, you don't have to be a fashion designer or a closeted actor. There are other courses available for you. Just like it's important for women to see successful business tycoons who are women or just to see a range of options open to them. What about me, somebody for whom traditional gay careers have no appeal whatsoever?

PLAYBOY: You managed to make it without any gay technology role models.

DENTON: Yeah, but maybe at a cost of feeling I had to make accommodations or choices between professional success and personal happiness—forced choices.

PLAYBOY: So by making it harder for leaders to stay in the closet, websites like yours are doing good by our gay sons and daughters. Once again, you side with the camp that says the internet is making our lives better and technology is propelling us toward a better future.

DENTON: It's not quite as simple as that. I think it will be generally good for the cause of social liberalism and recognizing each other's flawed but wonderful humanity. You can make a strong argument that Tim Berners-Lee and the dozen people who were involved at various critical stages of the development of the web did more good than all the foreign aid workers and all the liberal military interventions over the past 50 years. Think of a peasant who has historically been hoodwinked by middlemen on the price of his harvests, and now you're giving him the information he needs for a stronger negotiating position. Here you have somebody playing around with the operating system of the information economy. Actually, it's sort of accidental; some of the early pioneers didn't realize what they were doing, yet it's far more meaningful than any deliberate effort to help the poor. You could argue that Uber may do more for the planet than foreign aid workers in Mozambique because at some point some version of Uber will allow for more efficient use of resources and a better standard of living.

PLAYBOY: How does a taxi-hailing app help humanity?

DENTON: It's a great example of surge pricing. Any economist would tell you surge pricing is eminently sensible; if you cap prices, you stop a market from working in a way it could work. But it offends people's sense of fairness because surge pricing basically means we are rationing supply of this commodity, transport, at peak times to rich people, people who can afford it. It takes notional inequality and turns it into something concrete—the poor person is waiting in the rain for a taxi that will never come, and the rich person has a black Mercedes come scoop them up. But it's inevitable. It will happen everywhere, in every market.

PLAYBOY: How can you be so sure?

DENTON: Markets are more efficient mechanisms for the distribution of services. The only thing that happens if you don't have surge pricing in a city like New York is that the limos and the cars dry up at certain times. Then nobody gets anything. And maybe that's the point. Maybe the point is that human beings are not so much concerned with their well-being as with their relative position. If they can't have access to this thing that's in short supply, then they don't want anybody else to either.

PLAYBOY: What about Airbnb? That's a similar model—another so-called two-sided marketplace, except for lodging instead of transportation.

DENTON: It's the same thing, a clear economic benefit from underused resources such as empty apartments or drivers who don't have passengers. I like the idea of completely distributed marketplaces. Ultimately we'll see this idea applied to anything that can be quantified, authenticated, verified—whether it's limo service, media, information, retail. There's only gain to be had from making use of wasted resources. You do have the question of how to allocate the gain, but generally I believe in getting the gain and then arguing about the allocation.

PLAYBOY: What does that world look like, where everything is a perfectly efficient market and we're all both buyers and sellers?

DENTON: It will become more atomized. The Silicon Valley elite will control all the marketplaces. Uber, Amazon, Google—all these things are natural monopolies. There are massive network effects, as economists call them. The more drivers you have, the more passengers you'll get; the more passengers you get, the more drivers you'll have. And there will be room for only one player in every major category.

PLAYBOY: So we're moving back to an age of monopolies?

DENTON: Absolutely, there's no question about that. The political question is what you do about those monopolies.

PLAYBOY: Aren't monopolies inherently inefficient?

DENTON: Well, they result in income inequality, above all, and abuse of power. There's a concentration of power and wealth among the managers, owners and employees of monopolies, and usually the political system steps in to limit the power of those monopolies. But I'm pretty sure we'll end up with monopoly taxation or nationalization. That is ultimately the only answer to the concurrent concentration of power and money in this country—a Google tax.

PLAYBOY: Google will basically bribe the government not to break up its monopoly?

DENTON: Yeah. Or you can say the government will bully Google to the point that it either pays fines for its abuse of monopolistic behavior—the current random application of justice that seems to be landing on American banks—or you could have a better system. You could have a more systematic approach, which would be to have some kind of monopoly tax.

PLAYBOY: Google would effectively become a sort of government-sanctioned contractor or privatized agency.

DENTON: This is looking at Google as a utility. Look at electric utilities, gas, originally telecommunications, where there were network effects, where there were substantial investment costs or capital-intensive barriers to entry. These are classic criteria of a natural monopoly. It's going to be a monopoly, and to break up those companies would be absurd. If you break up Google, you'll need a whole other search-engine infrastructure. You're going to have to build all those server farms, and you're going to have a whole other team of information scientists working on the algorithms to improve searches. Yeah, you could try to create some kind of competition, but it would be absurd. So if they are natural monopolies, then the only question is, Who gets the monopoly profits, and who gets the monopoly power? Is it going to be the shareholders, or is it going to be society at large?

PLAYBOY: What will be the life-changing or society-changing technologies that we're just starting to see now?

DENTON: The internet is it for this century, maybe the next one too. People ask what comes next too quickly. To the extent there is some kind of message in the valuation that the market has given Twitter, it is that communication, information and media are at the heart of this phase, this cycle, and it's a long, long cycle that could last 50 or 100 years. When you have an innovation as profound as the networking of sentient beings.… Those delusional futurists who talked about Gaia, the planetwide intelligence? They were spot-on. It's totally happening, and everything else comes out of that.

PLAYBOY: By "everything else," do you mean wearable computing, self-driving cars and that stuff?

DENTON: Who gives a fuck about wearable computing? That's just a detail. I mean improvement in biotech, curing cancer, efficient travel into orbit, better device storage, solving carbon emissions. All these other problems will be solved by the internet by harnessing the collective intelligence. Everything else will fall out with that.

PLAYBOY: That definitely sounds utopian. To be clear, you just said the internet is going to solve global warming, correct?

DENTON: Yeah. Intelligence connected to human beings will achieve rates of technological progress that would have been impossible in previous eras. Of course we'll solve problems more quickly.

PLAYBOY: So the solution to global warming will be a technological fix?

DENTON: It might be a technological fix for capturing carbon or getting off the planet or coming up with nonpolluting fuels.

PLAYBOY: But it's not going to be a political fix?

DENTON: No.

PLAYBOY: It's not going to be everybody growing up and saying, "We need to do this"?

DENTON: Oh, no. I think a good strategy in life is to wait until you have a good solution. Wind power, hybrid fuel trains—these are partial solutions. No one thinks they're viable. No one thinks they're going to solve the problem. They're basically token approaches. Now, sometimes a token approach can get people thinking, and maybe it starts to develop a technology that will ultimately be economically viable, but usually not. Usually it's better to say, "Okay, this is a problem and it needs to be monitored. But we don't have an answer for it right now, so let's come back to it in five, 10 or 15 years, when we might have a better answer." I don't think that's necessarily irresponsible.

PLAYBOY: So you're an optimist about technological change but a cynic about political change.

DENTON: I think technological change is going to be great for the rejuvenation of decrepit economic systems like that of the United States. This country is encrusted with privilege, mediocrity. It has early signs of sclerosis. This society needs a big jolt. It needs a big cleansing.

PLAYBOY: "Cleansing" sounds ominous.

DENTON: I mean in business and politics. I don't think you'll find many people who disagree with that now. This country, even in the tech sector, is full of people who are on this merry-go-round, who know the right headhunters and basically pass each other jobs as if they were a trade union with the sole rights to these positions in which they demand $500,000 a year. They move around from start-up flip to start-up flip. They're not incompetent; they're just not that good. These are the midlevel scandals. If you can industrialize gossip, if you can make it truly scale, you can expose all the mediocrity and incompetence. Now you've actually done something.

PLAYBOY: That's Pandora's box. It would be terrifying to open.

DENTON: It would be fantastic. People would actually have to work, and they'd have to be good. It would be great. Do you know how many lies there are? Every single time people are given the latitude to cheat and there's no one watching, no regulator and no mechanism for whistle-blowers, you get lies. Don't you ever get overwhelmed by the sheer amount of bullshit?

PLAYBOY: Is that because of our broken institutions, or is that just human nature?

DENTON: There's an accretion of bullshit, like an accretion of junk DNA in DNA, or fatty deposits in arteries. If you want to move things on without having a completely destructive revolution, you need some mechanism to put a big fucking shock in the system. I came to this country because I thought it was something, you know? And yet I'm more in love with the idea of the United States than I am with the reality.

PLAYBOY: The idea being?

DENTON: Permanent revolution. Nothing is sacred. The United States is distributed; it's resilient. There's lots of redundancy built in, and it's big enough that no establishment can control everything.

PLAYBOY: So the idea you came here for is true, but it's not as true as you believe it will be in the future.

DENTON: The web is a deeply American idea. The web is saving the United States from sclerosis.

PLAYBOY: You're somebody whose intelligence straddles two worlds, the liberal-arts world and the engineering-systems-based world. Did that shape your career?

DENTON: There is definitely a type, like a Mark Zuckerberg, who applies a logical way of thinking to the social grid. I think that's pretty consistent among people who have done well in social media. They're basically geeks who made their accommodation, who actually survived high school. Not instinctively but just through sheer force of will and intellect, they made themselves understand the system—who had the power in high school and who you needed to align yourself with and how to do it.

PLAYBOY: And that's you?

DENTON: I went to this weird school as a kid, a Montessori school run by a couple of American hippies who didn't believe in age-defined streaming. It was a very small school, so basically I had no contemporaries. I had no early socialization. I was with kids quite a few years older than I was. When I first went to a regular school, at the age of 11, I was completely unqualified to handle the environment.

PLAYBOY: What did you do?

DENTON: I was quiet for two years, and I barely had a friend by about year three.

PLAYBOY: You have one sibling?

DENTON: I have a younger sister.

PLAYBOY: What were you like as a kid?

DENTON: Smart, bratty, arrogant. Compensating arrogance, compensating for a bit of insecurity. I liked hanging out with adults.

PLAYBOY: Are you more like one of your parents than the other?

DENTON: I was closer to my mom. She was social and very determined. She was a refugee from Hungary, both she and her mother, who'd been brought up in Vienna in a Jewish orphanage. Both of them were tough characters. My mom was in the Budapest ghetto during the war, and I think she was one of those kids who had to be stronger than the adults. The adults were falling apart, and she basically couldn't afford to be a kid, you know? My grandmother's husband died in a labor camp, and she survived by having lovers. I was always more drawn to that side of the family. I had mixed feelings about my dad. My mother was a social organizer; I definitely got that from her. She was always fixing things, like arranging for people to go and interview for jobs. She was a matchmaker.

PLAYBOY: When did you decide that London didn't fit your plans?

DENTON: I've been away from the U.K., away from London, since I was 18. I went to Eastern Europe when I was 23. Since then I've lived in the U.K. for maybe two years.

PLAYBOY: And you came out when you were in college?

DENTON: After college. I mean, I wasn't fully out until I was out to my parents. If you're not out to your parents, then you have to maintain this protective zone around them. Gay guys spend a lot of time and effort coming out. There's a lot of calculation. You have to be aware about social networks and who's how many degrees away from somebody else, and you have to be aware of the speed with which gossip will be transmitted. You have to maintain a proper buffer around the people you're trying to protect.

PLAYBOY: Is that what got you interested in the mechanics of gossip?

DENTON: It's possible. It's a hypothesis.

PLAYBOY: So when were you fully out?

DENTON: With friends, probably in my late 20s. In Budapest I wasn't out. I was in Budapest from 23 to 28, and it's a pretty homophobic place.

PLAYBOY: When you eventually came out to your parents, was there any family strife?

DENTON: There was a lot of family drama. The thing that was sad was my mom became sick with cancer very soon after, so everything stopped. Everything was frozen, unresolved. No one wanted to upset her. That was a miserable period. I was on the West Coast. I'm kind of amazed I actually managed to come through that. My mom was sick, and we knew she was dying. She had two years from diagnosis to death, and I was in San Francisco. I flew back once a month. It was tough on my mom because my sister and my dad both shut down. That's what they did. My mom was super strong. I never saw her cry. I saw her cry at other times, but not through that. She would say, "I'm not afraid."

PLAYBOY: Is it safe to assume that was the worst period of your life?

DENTON: Yeah, and I was out of my depth doing two start-ups, First Tuesday and Moreover.

PLAYBOY: You did those at the same time?

DENTON: Yeah. I started First Tuesday while we were working on Moreover because the coding was going on and I didn't really have enough to do during that. It was wildly overhyped. At one point they thought it was going to be a billion-dollar company. This was even after the Nasdaq had crashed.

PLAYBOY: How much did you sell it for?

DENTON: The nominal price was $60 million, I think. The cash component was less. The stock turned out to be worthless.

PLAYBOY: For something that was basically—

DENTON: A party. But cool people went to the parties. If you were in the venture market at the time, if you had a cool start-up or were a cool venture capitalist, you had to be there. At some point it got so big there would be 2,000 people and four or five TV cameras at the events. It was crazy. And I saw what happened. You get what you deserve, you know? In press coverage and attention, whatever you get undeservedly on the way up, you will pay a price for. If they put you on the front cover before you've actually done anything, they will pull you down as brutally as they were enthusiastic in pushing you up. There's a kind of karma that obtains in media coverage.

PLAYBOY: What's your relationship to money? What does it mean to you?

DENTON: Mainly it gives me the joy of being free. It gives me the freedom I always wanted. Everything I am is a result of not caring about social convention and not having to worry about money. I can say whatever I want. The times I'm holding back in this conversation are only to protect other people's feelings. And not even that much. But you only have that kind of freedom, and our writers only really have that freedom—in theory—if they actually have the economic circumstances to allow that.

PLAYBOY: People have crazy ideas about what enough money is, though.

DENTON: Well, we have to be profitable, and I get paid a decent salary now. It's very recent. For a long time I was taking $60,000 a year.

PLAYBOY: Until how recently?

DENTON: Until two years ago.

PLAYBOY: Gawker is famous for popularizing the ultra-low-wage model for journalism, paying writers as little as $12 per article for the first couple of years.

DENTON: That reputation has haunted me. At the very beginning there was no revenue, no advertising. This was basically money out of my pocket. So I would do a simple calculation. I would take the amount of money I had and divide it by costs, and I could keep going for 10 years. I didn't need to make any money for 10 years. Remember, when we started in 2002 there was nothing going on. People had written off the internet at that point. It was such a cataclysmic collapse.

PLAYBOY: At what point did you become confident Gawker was a real company, a real business that was going to make you a fair amount of money?

DENTON: I resisted that. I never thought, This is going to make me a fair amount of money. I think at some point I realized, Oh, this can pay for itself.

PLAYBOY: How long will you keep running your current company before seeking what venture capitalists call a "liquidity event"?

DENTON: Oh, this one's long. How long was Steve Jobs thinking about smartphones before he actually launched one? Twenty years? Twenty years waiting and waiting and waiting. It's like the enemy is advancing, the guns are loaded, but the time's not right yet. I think that's what truly great leaders do. They marshal their resources, they train their troops and make sure they're well supplied, and then they wait for the right moment.

PLAYBOY: Who are the great leaders in technology now that Jobs is gone?

DENTON: There are some exceptional people. Evan Williams is an exceptional person. He doesn't present well, but he has an idea that is pretty much the same idea he's repeated again and again with Blogger, Twitter and Medium, only with different wrinkles. He's been the most influential person in web publishing, but I don't think he's ever done anything cheaply or cynically. He deserves the success. There's nothing more to him. He's just a believer in simple, awesome tools that help people communicate.

PLAYBOY: Who else?

DENTON: Marc Andreessen is obviously extremely smart and bold. I admire the fact that he's all-in on this bet that the internet is changing everything, every industry. He's an absolute extremist, but actually that's a rational position to take. [Venture capitalist] Fred Wilson is smart and nice and probably in a position to be more truthful than any of the others. And Mark Zuckerberg, obviously: canny, determined, has retained enough power at Facebook. He's going to have another 20, 30, 40 years of being productive, being in charge of the company and being able to do things.

PLAYBOY: Now that you've become part of the establishment, do you feel more sympathy for Gawker's targets?

DENTON: I don't feel like part of the establishment. I don't even know whether there is an establishment. From up close, the establishment isn't up to much. Celebrity was a better deal 50 years ago. There was a time, as long as you weren't having orgies—or as long as you were discreet about your orgies—and as long as you weren't a Communist, you were probably fine. You'd be lionized and could get all the pussy you wanted.

PLAYBOY: Speaking of the establishment, what will The New York Times look like in 10 years? Will it exist? Will the Sulzberger family still own it, or will they have sold it, perhaps to Michael Bloomberg?

DENTON:The New York Times will exist. Someone else will own it. Most families, the more generations they are from the original founder, the more fragmented the ownership, and eventually the nephews, grandnieces and great-great-grandchildren want their money now. They'd rather take the purchase price than zero dividends. I think the Times has bottomed out, and now, even though the signs are mixed, it will be able to put on more in digital revenue than it loses in print. Or I hope so, because I like the Times. There should be at least one or two survivors. Even when a major disaster kills most life on earth, usually a few species survive. Dinosaurs survived and became birds. Maybe that's the future of The New York Times: It will be the survivor of the dinosaurs, the little tweeting thing you see flying around.

PLAYBOY: If you're Jeff Bezos, what do you do with The Washington Post?

DENTON: Obviously you apply the Amazon recommendation engine. The interesting move would be to see whether you could take an entire newspaper-reading population and wean them off print. The price of Kindles is coming down. How much would it cost to bundle a Kindle with your subscription to The Washington Post? Discontinue the print and, as a gift, give everybody a Washington Post reader that can also buy books for them. That's what I'd do. That's what Bezos would do if he were ballsy.

PLAYBOY: Do you know him at all?

DENTON: No, though I had a dream that he had acquired us.

PLAYBOY: What would you do if you picked up the phone and he was on the other end, saying he wanted to buy Gawker Media?

DENTON: Amazon's the only company…. Well, I also like the idea of News Corp. Buccaneering was a word I always liked to describe Gawker Media.

PLAYBOY: Rupert Murdoch had the same notions about News Corp, to the point that he reportedly considered adopting a pirate ship as the company's logo. Do you feel a kinship with Murdoch?

DENTON: That sounds arrogant. I think he's done four amazing things, and most people get only one: Fox Network, Fox News, satellite TV in the U.K. and breaking the print unions. He saved Fleet Street. He saved London's newspaper industry.

PLAYBOY: What about Tina Brown? Is she done? Have we seen the last of her?

DENTON: I don't know about that. She has a tough rap. Was her Newsweek really that bad? Her biggest problem has been that she was dependent on the goodwill of media proprietors—Si Newhouse, Harvey Weinstein and then Barry Diller. And a media proprietor, particularly a late-era media proprietor, is a fundamentally dysfunctional businessman. There was a time when media made money and rational businesspeople would go into it. In an era when media basically doesn't make money, the only businessman who would go into it would be some kind of egomaniac, like me. [laughs] If I were truly into the money, I'd be in waste disposal or something like that. I'd be in some unglamorous profession. Media is way overpopulated. So she's dependent on the goodwill and the external financial resources of these erratic, aging proprietors.

PLAYBOY: You didn't always plan to be a media proprietor. You had notions of entering politics at one point.

DENTON: As a 16-year-old political nerd I wrangled myself a research position for the Social Democratic Party, which was a Labour splinter party. I quickly recognized that I wouldn't be electable. After that I wanted to be one of those shadowy, behind-the-scenes operatives, like a Lee Atwater or a Karl Rove.

PLAYBOY: It's easy to picture you as a pretty good Karl Rove.

DENTON: Oh, I'd be very good. I'd be so good! [laughs] I'd fight dirty in the interest of good causes. I almost had a whole campaign for a gas tax. Syphilitic Saudi sheiks, American women despoiled—basically taking our money from the gas station to fund their debauched sex lives, their despoiling of our women and terrorist attacks against our country. I don't frame it as an environmental cause. You've won the environmentalists already. You're trying to win the swing voters, the kind of people who don't like our money going to our enemies. So you make the campaign about that. No environmentalists—they're way too prissy to want to win. That's what I hate about liberals in this country. I hate them so much.

PLAYBOY: You do? You hate them?

DENTON: I hate liberals in this country so much because they're so fucking prissy. Did you ever see that documentary about Lee Atwater, Boogie Man? Lee Atwater was a terrible man. The Willie Horton campaign is a stain on the Republican Party, on the Bush family—let that all be stipulated. But you see in this movie that he has such joy in the battle, in the struggle, in the game, you know? He loves it. There are interviews with Michael Dukakis 20 years later, and Dukakis still cannot understand what happened. He still doesn't know how he got beat. This whiny, prissy—who would you want to work with? Who would you want to have beside you in the foxhole? Atwater is way more fun, probably a way better colleague, with way more appetite to win.

PLAYBOY: Isn't that a stereotype, the wimpy liberal? What about Barack Obama and his gang of tough Chicago politicos?

DENTON: In his own slightly bloodless way, he has competitive people. Obama himself is pretty competitive, and there are different ways of playing the game, right? It doesn't all need to be dirty South Carolina politics. That said, my political hero is Lyndon Johnson. I love people who are prepared to do what it takes, who aren't squeamish. If you want to stay pure, never break a story and never fuck anyone.

PLAYBOY: You got engaged recently. Have you always wanted to get married?

DENTON: No. My personal narrative was that I didn't want to get married in general; I just wanted to get married to Derrence. I'm marrying an individual. I'm not endorsing an institution. But two years ago, we had a party to benefit gay marriage—I think it was right around the date when it passed in New York—and apparently I said there that I wanted to get married because gay relationships ended too easily. I hadn't remembered saying that; someone reminded me recently. [laughs] I was just coming off a breakup that had taken all of three days to implement—no kids, no jobs, no pets, no nothing. Relationships are hard enough and likely enough to fray, so one needs some kind of glue, some ritual in front of friends and family and the state to ensure that at least there's a cooling-off period before you actually break up.

PLAYBOY: Is that part of why you want to get married now?

DENTON: No. It's that this is as good as it's going to get. Isn't that the key? It doesn't sound very romantic, but when I saw my apartment, I knew it was much better than anything else. It was maybe 30 percent more than I wanted to pay, but it was 200 percent better than anything else I'd seen. I had to contain the expression on my face, because what I was thinking was, Yes, this is the one. That's how I felt with Derrence.

PLAYBOY: That's not a very romantic metaphor.

DENTON: I think it's actually a very real metaphor when you're with somebody in a better relationship than you ever expected or hoped for in your life and by far better than anything you could ever imagine with anybody else. Yeah, hypothetically, theoretically, there might be somebody else out there for me, but I don't have 100 lifetimes to go find him. So this is the best person I could be with in this lifetime.

PLAYBOY: How did you meet?

DENTON: How did we meet? [laughs]

PLAYBOY: Yes.

DENTON: [Laughs] I think you can say on the record that I knew his boyfriend.

PLAYBOY: The New York Post's gossip column reported at the time that the boyfriend you're referring to threw a brick through your window.

DENTON: It was a stone, not a brick. I actually gave them the whole backstory. I knew they couldn't do anything with it.

PLAYBOY: Why couldn't they?

DENTON: Too complicated. The mainstream press doesn't really want gay gossip. They can't even deal with closet cases. It's a mixture of lingering distaste for the homosexual act and a modern version of correctness. They don't even know whether outings are politically correct or not. So they're completely paralyzed. They do not know how to deal with gay guys. They're just about getting to be able to deal with, say, a gay engagement being news. But the true pansexual messiness of most gay sexual histories is not something they or their readers are ready for.

PLAYBOY: Which is funny, because "pansexual messiness" sounds more interesting than most of what you read in the gossip pages.

DENTON: Well, I think everybody is more interesting than how they're portrayed.

PLAYBOY: Do you ever have misgivings about exposing people's private lives, their sex lives?

DENTON: If there's a gap between your private behavior and your public status, that's what makes the story for us. To my mind, the only real modern sin is hypocrisy.

*Editor's note: The original version of this article stated Gawker launched before Gizmodo, however, Gizmodo was the first site in Gawker Media's portfolio.